Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions.

Experimental results from entries 7–9 in Table 1 present a decreasing trend of the trans/cis ratios without obvious difference between C -2-nitrophenylimine 2a and C -3- and 4-nitrophenylimines 2b and 2c , revealing that the ortho -nitro effect does not exist in the sulfa-Staudinger cycloadditions involving other alkanesulfonyl chlorides, such as phenylmethanesulfonyl chloride ( 1c ).

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